DE2951349A1 - NAPHTHALINTETRACARBONSAEUREDIIMIDES AS ELECTRIC SEMICONDUCTORS AND PHOTO LADDERS - Google Patents
NAPHTHALINTETRACARBONSAEUREDIIMIDES AS ELECTRIC SEMICONDUCTORS AND PHOTO LADDERSInfo
- Publication number
- DE2951349A1 DE2951349A1 DE19792951349 DE2951349A DE2951349A1 DE 2951349 A1 DE2951349 A1 DE 2951349A1 DE 19792951349 DE19792951349 DE 19792951349 DE 2951349 A DE2951349 A DE 2951349A DE 2951349 A1 DE2951349 A1 DE 2951349A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- naphthalintetracarbonsaeurediimides
- ladders
- photo
- semiconductors
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000004065 semiconductor Substances 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 4
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 C 1 -C 4 -alkyl Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 150000005838 radical anions Chemical class 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- VUGRRXJWUGXPGM-UHFFFAOYSA-N 1-(hexylamino)pyrrolidin-2-one Chemical compound CCCCCCNN1CCCC1=O VUGRRXJWUGXPGM-UHFFFAOYSA-N 0.000 description 1
- GSOFREOFMHUMMZ-UHFFFAOYSA-N 3,4-dicarbamoylnaphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=N)C(C(=N)O)=C(C(O)=O)C(C(O)=O)=C21 GSOFREOFMHUMMZ-UHFFFAOYSA-N 0.000 description 1
- RJCHVBHJXJDUNL-UHFFFAOYSA-N 5,8-dicarbamoylnaphthalene-1,4-dicarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=N)O)=CC=C(C(O)=N)C2=C1C(O)=O RJCHVBHJXJDUNL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000615 nonconductor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
- G03G5/0651—Heterocyclic compounds containing two or more hetero rings in the same ring system containing four relevant rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
-ι--ι-
BAYER AKTIENGESELLSCHAFT 5090 Leverkusen, BayerwerkBAYER AKTIENGESELLSCHAFT 5090 Leverkusen, Bayerwerk
Zentralbereich G/Rz \ qCentral area G / Rz \ q
Patente, Marken und Lizenzen 'Patents, trademarks and licenses'
Naphthalintetracarbonsäurediimide als elektrische Halbleiter und PhctoleiterNaphthalene tetracarboxylic acid diimides as electrical semiconductors and phctoconductors
Gegenstand der Erfindung ist die Verwendung von Naphthalintetracarbonsäurediimiden der Formel IThe invention relates to the use of naphthalenetetracarboximides of the formula I.
R,R,
R-R-
worinwherein
R ein gesättigter oder olefinisch ungesättigter aliphatischer oder cycloaliphatischer Rest ist, vorzugsweise mit bis zu 12, insbesondere mit bis zu 6 C-Atomen, der eine Elektronendonatorgruppe enthalten muß, undR is a saturated or olefinically unsaturated aliphatic or cycloaliphatic radical, preferably with up to 12, in particular with up to 6 carbon atoms, which must contain an electron donor group, and
die Reste R1, unabhängig voneinander, Wasserstoff, C1-C4-AIkYl, Halogen, NO2, SO^H, CN, COOR2, NR2 (R = Wasserstoff, C^-C^-Alkyl), Hydroxyl, C^-C^- Alkoxy bedeuten,the radicals R 1 , independently of one another, hydrogen, C 1 -C 4 -alkyl, halogen, NO 2 , SO ^ H, CN, COOR 2 , NR 2 (R = hydrogen, C ^ -C ^ -alkyl), hydroxyl, Mean C ^ -C ^ - alkoxy,
als elektrische Halbleiter oder Photoleiter.as electrical semiconductors or photoconductors.
Le A 19 979Le A 19 979
130027/0207130027/0207
Elektronendonatorgruppe in den Resten R kann ein Heteroatom sein, wie -0-, -S- oder -NR^- (R^ = Wasserstoff, C1-Cg-AIkYl oderCR-5O mit R^ = Wasserstoff, C1-C12-AIkVl tzw. Cj-C^-Alkylen). -NR- kann für R = Wasserstoff, C1-Cg-AIkYl nach Umsetzung mit einer anorganischen oder organischen Säure bzw. mit einem Alkylierungsmittel auch als Ammonium-Ion -NIrR- mit R = Wasserstoff, C1-C^ und einem anorganischen bzw. organischen Anicn einschließlich dem Radikal-Anion des Tetracyanochinodimethans (TCNQ) vorliegen, wobei im Falle des TCNQ neben dem Radikal-Anion noch eine äquivalente Menge neutrales TCNQ vorliegen kann.Electron donor group in the radicals R can be a heteroatom, such as -0-, -S- or -NR ^ - (R ^ = hydrogen, C 1 -Cg -AlkYl or CR- 5 O with R ^ = hydrogen, C 1 -C 12 -AIkVl or Cj-C ^ -alkylene). -NR- can for R = hydrogen, C 1 -Cg -AlkYl after reaction with an inorganic or organic acid or with an alkylating agent as an ammonium ion -NIrR- with R = hydrogen, C 1 -C ^ and an inorganic or Organic anions including the radical anion of tetracyanoquinodimethane (TCNQ) are present, it being possible for an equivalent amount of neutral TCNQ to be present in addition to the radical anion in the case of TCNQ.
Besonders geeignet für die Verwendung als Halbleiter oder Photoleiter sind Naphthalin-1.4.5.8-tetracarbcnsäurediimide mit R = -(CH2)X-N(CH3)2 mit χ = 2 - 12Particularly suitable for use as semiconductors or photoconductors are naphthalene-1.4.5.8-tetracarbic acid diimides with R = - (CH 2 ) X -N (CH 3 ) 2 with χ = 2-12
τ2;χ - N^J mit χ = 2, 3, 4 und 6 τ 2 ; χ - N ^ J with χ = 2, 3, 4 and 6
O
-CH2-CH2-OH bzw. -CH2-CH2-OCH3 O
-CH 2 -CH 2 -OH or -CH 2 -CH 2 -OCH 3
-CH2-CH2-S-CH3 -CH 2 -CH 2 -S-CH 3
Die spezifische Leitfähigkeit typischer organischer Verbindungen ist kleiner als 10 Ohm"1 eic" , so daß sie elektrische Isolatoren sind. Die erfindungsgemäß zu verwendenden Stoffe haben dagegen spezifische Leitfähigkeiten vonThe specific conductivity of typical organic compounds is less than 10 ohms " 1 eic", so that they are electrical insulators. In contrast, the substances to be used according to the invention have specific conductivities of
-12(1-1 —1
10 uu cm , die bei Belichtung noch um einen Faktor-12 (1-1-1
10 uu cm, which with exposure still by a factor
2 bis 100 größer werden. Demnach sind diese Substanzen insbesondere geeignet für Reproduktionstechniken wie z.B. zur Herstellung von Photokopien, sowie für optoelektronische Bauelemente wie z.B. Photozellen, Lichtschranken u.a.2 to 100 become larger. Accordingly, these substances are particularly suitable for reproductive techniques such as e.g. for the production of photocopies, as well as for optoelectronic components such as photocells, light barriers i.a.
Le A 19 979Le A 19 979
130027/0207130027/0207
Die erfindungsgemäß zu verwendenden Substanzen sind bekannt, z.B. aus den DE-AS 1 230 031; 1 195 762; und den DE-OS 1 445 768 und 1 445 769.The substances to be used according to the invention are known, for example from DE-AS 1 230 031; 1,195,762; and DE-OS 1 445 768 and 1 445 769.
710 Gew.-Teile Naphthalin-1,4,5,8-tetracarbonsäure und 830 Gew.-Teile N-Hexylamino-pyrrolidon werden in 1900 Vol.-Teilen Dimethylformamid 2 Stunden unter Rückfluß zum Sieden erhitzt. Nach dem Abkühlen filtriert man, wäscht den Rückstand mit Dimethylformamid, dann mit Ether und erhält 1270 Gew.-Teile des Diimids II:710 parts by weight of naphthalene-1,4,5,8-tetracarboxylic acid and 830 parts by weight of N-hexylaminopyrrolidone in 1900 parts by volume of dimethylformamide for 2 hours Reflux heated to boiling. After cooling, it is filtered, the residue is washed with dimethylformamide, then with ether and receives 1270 parts by weight of the diimide II:
Die Mikrowellenleitfähigkeitsmessung am Pulver ergibt eine Dunkelleitfähigkeit von '^0,3 . 10~ Ohm~ cm" Nach 20 Minuten Belichten mit einer Xenonhochdrucklampe steigt die Leitfähigkeit auf 0,55 . 10~3 Ohm"1 cm" an (Meßfrequenz 9 GHz).The microwave conductivity measurement on the powder shows a dark conductivity of '^ 0.3. 10 ~ ohm ~ cm "After 20 minutes of exposure to a xenon high-pressure lamp, the conductivity increases to 0.55. 10 ~ 3 ohms" 1 cm "(measuring frequency 9 GHz).
Das analog Beispiel 1 hergestellte Diimid III zeigtThe diimide III prepared analogously to Example 1 shows
-3 -1 -1 eine Dunkelleitfähigkeit von ^0,3 . 10 Ohm cm die nach 20-minütigem Belichten auf 5,5 . 10 Ohm cm (Mikrowellenleitfähigkeitsmessung) ansteigt:-3 -1 -1 a dark conductivity of ^ 0.3. 10 ohm cm that after 20 minutes of exposure to 5.5. 10 Ohm cm (microwave conductivity measurement) increases:
Le A 19 Le A 19 979979
130027/020?130027/020?
-S--S-
0UrW 0 UrW
(CH3)2N-(CH2)2-N V=< y(CH 3 ) 2 N- (CH 2 ) 2 -NV = <y
Das analog Beispiel 1 aus dem Naphthalin-1,4,5,8-tetracarbonsäuredianhydrid hergestellte Diimid IV zeigt eine Dunkelleitfähigkeit (pulverförmige Probe, Mikrowellenleitfähigkeitsmessung, Meßfrequenz 9 GHz) von 1,9 . 10~ Ohm ~ cm" , die nach 20-minütigem Belichten mit einer Xenonhochdrucklampe auf 67 · 10"*·^ Ohm" cm"' ansteigt.The analogous to Example 1 from the naphthalene-1,4,5,8-tetracarboxylic acid dianhydride produced diimide IV shows a dark conductivity (powdery sample, Microwave conductivity measurement, measuring frequency 9 GHz) of 1.9. 10 ~ ohm ~ cm ", which after 20 minutes Exposure with a high pressure xenon lamp to 67x10 "* * ^ Ohm "cm" 'increases.
(CH3) 2N-(CH2) 10-nV=/Ä-(CH2J10-N (CH3) 2 (IV)(CH 3 ) 2 N- (CH 2 ) 10 -nV = / Ä- (CH 2 J 10 -N (CH 3 ) 2 (IV)
Die erfindungsgemäßen Diimide lassen sich als optoelektronische Bausteine in elektronischen Schaltelementen bzw. als Photoleiter in Reproduktionsgeräten anwenden.The diimides according to the invention can be used as optoelectronic Use components in electronic switching elements or as photoconductors in reproduction devices.
Le A 19 979Le A 19 979
130027/0207130027/0207
Claims (1)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792951349 DE2951349A1 (en) | 1979-12-20 | 1979-12-20 | NAPHTHALINTETRACARBONSAEUREDIIMIDES AS ELECTRIC SEMICONDUCTORS AND PHOTO LADDERS |
| DE8080107719T DE3065326D1 (en) | 1979-12-20 | 1980-12-08 | Naphthaline-tetracarbonic acid diimides as electrical semiconductors and photoconductors |
| EP80107719A EP0031065B1 (en) | 1979-12-20 | 1980-12-08 | Naphthaline-tetracarbonic acid diimides as electrical semiconductors and photoconductors |
| JP17731280A JPS5695241A (en) | 1979-12-20 | 1980-12-17 | Naphthalene tetracarbonic acid diimide as semicondctor and photoconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792951349 DE2951349A1 (en) | 1979-12-20 | 1979-12-20 | NAPHTHALINTETRACARBONSAEUREDIIMIDES AS ELECTRIC SEMICONDUCTORS AND PHOTO LADDERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2951349A1 true DE2951349A1 (en) | 1981-07-02 |
Family
ID=6089043
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792951349 Withdrawn DE2951349A1 (en) | 1979-12-20 | 1979-12-20 | NAPHTHALINTETRACARBONSAEUREDIIMIDES AS ELECTRIC SEMICONDUCTORS AND PHOTO LADDERS |
| DE8080107719T Expired DE3065326D1 (en) | 1979-12-20 | 1980-12-08 | Naphthaline-tetracarbonic acid diimides as electrical semiconductors and photoconductors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080107719T Expired DE3065326D1 (en) | 1979-12-20 | 1980-12-08 | Naphthaline-tetracarbonic acid diimides as electrical semiconductors and photoconductors |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0031065B1 (en) |
| JP (1) | JPS5695241A (en) |
| DE (2) | DE2951349A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0224779A1 (en) * | 1985-11-30 | 1987-06-10 | Bayer Ag | Radical anion salts of 1,4,5,8-naphthalenetetracarboxylic acid derivatives, process for their preparation, and their use |
| US7569693B2 (en) | 2006-06-12 | 2009-08-04 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| US7671202B2 (en) | 2004-01-26 | 2010-03-02 | Northwestern University | Perylene n-type semiconductors and related devices |
| US7893265B2 (en) | 2007-01-08 | 2011-02-22 | Polyera Corporation | Methods for preparing arene-BIS (dicarboximide)-based semiconducting materials and related intermediates for preparing same |
| US7902363B2 (en) | 2006-11-17 | 2011-03-08 | Polyera Corporation | Diimide-based semiconductor materials and methods of preparing and using the same |
| US7947837B2 (en) | 2006-10-25 | 2011-05-24 | Polyera Corporation | Organic semiconductor materials and methods of preparing and use thereof |
| US8022214B2 (en) | 2007-01-24 | 2011-09-20 | Polyera Corporation | Organic semiconductor materials and precursors thereof |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02244058A (en) * | 1988-10-05 | 1990-09-28 | Minolta Camera Co Ltd | photoreceptor |
| JPH02305886A (en) * | 1989-05-19 | 1990-12-19 | Nec Corp | Organic thin-film el element |
| JPH0380887A (en) * | 1989-08-23 | 1991-04-05 | Akira Ishikawa | Manufacture of sleeping pad |
| US5468583A (en) * | 1994-12-28 | 1995-11-21 | Eastman Kodak Company | Cyclic bis-dicarboximide electron transport compounds for electrophotography |
| WO2002040479A1 (en) * | 2000-11-14 | 2002-05-23 | Shionogi & Co., Ltd. | Anti-helicobacterial agents |
| WO2003095453A1 (en) * | 2002-05-13 | 2003-11-20 | Shionogi & Co., Ltd. | Compounds against helicobacter activity |
| US7579619B2 (en) | 2005-04-20 | 2009-08-25 | Eastman Kodak Company | N,N′-di(arylalkyl)-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| US7629605B2 (en) | 2005-10-31 | 2009-12-08 | Eastman Kodak Company | N-type semiconductor materials for thin film transistors |
| US7422777B2 (en) | 2005-11-22 | 2008-09-09 | Eastman Kodak Company | N,N′-dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as n-type semiconductor materials for thin film transistors |
| DE102005061997A1 (en) * | 2005-12-23 | 2007-07-05 | Basf Ag | New naphthalene compound useful, e.g. in semiconductors, preferably organic field effect transistor and photovoltaic units and as UV-absorber and optical brightener |
| US7804087B2 (en) * | 2006-12-07 | 2010-09-28 | Eastman Kodak Company | Configurationally controlled N,N'-Dicycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as N-type semiconductor materials for thin film transistors |
| US7858970B2 (en) * | 2007-06-29 | 2010-12-28 | Eastman Kodak Company | Heterocycloalkyl-substituted naphthalene-based tetracarboxylic diimide compounds as N-type semiconductor materials for thin film transistors |
| US8380109B2 (en) * | 2008-01-11 | 2013-02-19 | Ricoh Company, Ltd. | Image forming apparatus and process cartridge |
| JP5392461B2 (en) * | 2008-01-17 | 2014-01-22 | 株式会社リコー | Electrophotographic equipment |
| JP5733612B2 (en) * | 2011-03-08 | 2015-06-10 | 国立大学法人信州大学 | Material for organic semiconductor thin film, method of forming organic semiconductor thin film using the material, and organic thin film transistor |
| KR102282494B1 (en) | 2014-08-28 | 2021-07-26 | 삼성전자주식회사 | Organic photoelectronic device and image sensor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1230031B (en) * | 1964-06-05 | 1966-12-08 | Bayer Ag | Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimide |
| DE2059540C3 (en) * | 1970-12-03 | 1985-05-15 | Hoechst Ag, 6230 Frankfurt | Electrophotographic recording material with a photoconductive layer |
| DE2636421A1 (en) * | 1976-08-13 | 1978-02-16 | Basf Ag | ELECTRICALLY CONDUCTIVE PERYLENE DERIVATIVES |
-
1979
- 1979-12-20 DE DE19792951349 patent/DE2951349A1/en not_active Withdrawn
-
1980
- 1980-12-08 EP EP80107719A patent/EP0031065B1/en not_active Expired
- 1980-12-08 DE DE8080107719T patent/DE3065326D1/en not_active Expired
- 1980-12-17 JP JP17731280A patent/JPS5695241A/en active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0224779A1 (en) * | 1985-11-30 | 1987-06-10 | Bayer Ag | Radical anion salts of 1,4,5,8-naphthalenetetracarboxylic acid derivatives, process for their preparation, and their use |
| US4841073A (en) * | 1985-11-30 | 1989-06-20 | Bayer Aktiengesellschaft | Radical anion salts of derivatives of 1,4,5,8-naphthalenetetracarboxylic acid and their use |
| US7671202B2 (en) | 2004-01-26 | 2010-03-02 | Northwestern University | Perylene n-type semiconductors and related devices |
| US7982039B2 (en) | 2004-01-26 | 2011-07-19 | Northwestern University | N-type semiconductors and related devices |
| US7569693B2 (en) | 2006-06-12 | 2009-08-04 | Northwestern University | Naphthalene-based semiconductor materials and methods of preparing and use thereof |
| US7947837B2 (en) | 2006-10-25 | 2011-05-24 | Polyera Corporation | Organic semiconductor materials and methods of preparing and use thereof |
| US7902363B2 (en) | 2006-11-17 | 2011-03-08 | Polyera Corporation | Diimide-based semiconductor materials and methods of preparing and using the same |
| US7893265B2 (en) | 2007-01-08 | 2011-02-22 | Polyera Corporation | Methods for preparing arene-BIS (dicarboximide)-based semiconducting materials and related intermediates for preparing same |
| US8022214B2 (en) | 2007-01-24 | 2011-09-20 | Polyera Corporation | Organic semiconductor materials and precursors thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0031065B1 (en) | 1983-10-12 |
| EP0031065A3 (en) | 1982-01-20 |
| JPH0139098B2 (en) | 1989-08-18 |
| EP0031065A2 (en) | 1981-07-01 |
| DE3065326D1 (en) | 1983-11-17 |
| JPS5695241A (en) | 1981-08-01 |
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